Looking for new ideas for my next boat. I have some ideas based on my research, but don't want to bias anyone as I am curious what you all might recommend that perhaps I haven't thought of...

Type of hull: Monohull
Length: 35-40'
Crew: Singlehanded with WOL (woman of leisure). However want the boat to be able to accomodate the occasional 2-3 guests for a daysail or weekend trip.
Type of sailing: (here's where it gets tough) Mostly coastal cruising along gulf of Mexico & east coast, but want to safely be able to make extended cruises throughout entire caribbean, Bermuda, and South America. Also, want to be able to make daysails in hometown of Pensacola.
The Rub: I know I can't have it all, but... I am looking for a boat that isn't such a pig that it is uncomfortable to make daysails and island hop in the caribbean, but yet sturdy enough to feel safe making a bluewater trip to Bermuda or the southern part of the caribbean when I want to. Any thoughts??